| 词条 | Pentosidine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 422904283 | ImageFile=Pentosidine.png | ImageSize=200px | IUPACName=(2S)-2-Amino-6-[2-[[(4S)- 4-amino-5-hydroxy-5-oxopentyl]]-4-imidazo [4,5-b]pyridinyl]hexanoic acid | OtherNames= |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo=124505-87-9 | PubChem=119593 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 106787 | SMILES = C1=CN(C2=NC(=NC2=C1)NCCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N | InChI = 1/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1 | InChIKey = AYEKKSTZQYEZPU-RYUDHWBXBF | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = AYEKKSTZQYEZPU-RYUDHWBXSA-N | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 59951 |Section2={{Chembox Properties | C=17 | H=26 | N=6 | O=4 | Appearance= | Density=1.47 g/cm3 | MeltingPt= | BoilingPtC= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} Pentosidine is a biomarker for advanced glycation endproducts, or AGEs. It is a well characterized and easily detected member of this large class of compounds. BackgroundAGEs are biochemicals formed continuously under normal circumstances, but more rapidly under a variety of stresses, especially oxidative stress and hyperglycemia. They serve as markers of stress and act as toxins themselves. Pentosidine is typical of the class, except that it fluoresces, which allows it to be seen and measured easily. Because it is well characterized, it is often studied to provide new insight into the biochemistry of AGE compounds in general. BiochemistryDerived from ribose, a pentose, pentosidine forms fluorescent cross-links between the arginine and lysine residues in collagen. It is formed in a reaction of the amino acids with the Maillard reaction products of ribose.[1] Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins—advanced glycation endproducts—by non-enzymatic browning reactions with carbohydrates.[2][3][4] PhysiologyIn vivo, AGEs form pentosidine through sugar fragmentation. In patients with diabetes mellitus type 2, pentosidine correlates with the presence and severity of diabetic complications.[5]References1. ^{{cite journal |journal=Kidney International |year=1998|volume= 53|pages= 416–422 |doi=10.1046/j.1523-1755.1998.00756.x |url=http://www.nature.com/ki/journal/v53/n2/pdf/4490049a.pdf |title=Renal catabolism of advanced glycation end products: The fate of pentosidine |vauthors = Miyata T, Ueda Y, Horie K, Nangaku M, Tanaka S, van Ypersele de Strihou C, Kurokawa K |pmid=9461101 |issue=2}} {{biochem-stub}}2. ^{{cite journal |author1=DG Dyer |author2=JA Blackledge |author3=SR Thorpe |author4=JW Baynes | title= Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo| journal= J. Biol. Chem.|url=http://www.jbc.org/cgi/content/abstract/266/18/11654| volume= 266|issue= 18|pages= 11654–11660|date= Jun 1991 |pmid= 1904867|doi= |accessdate=2007-12-14}} 3. ^{{cite web |url=http://www.medscape.com/viewarticle/567316 |title=DHEA Restores Oxidative Balance in Type 2 Diabetes| author=Will Boggs| publisher=Medscape| accessdate=2007-12-14 |format= |website= |archiveurl = https://web.archive.org/web/20080107124413/http://www.medscape.com/viewarticle/567316 |archivedate = 2008-01-07}} 4. ^{{cite journal |vauthors=Meerwaldt R, Graaff R, Oomen PH, etal |title=Simple non-invasive assessment of advanced glycation endproduct accumulation |journal=Diabetologia |volume=47 |issue=7 |pages=1324–30 |year=2004 |pmid=15243705 |doi=10.1007/s00125-004-1451-2 }} 5. ^{{cite journal |title=Pentosidine formation in skin correlates with severity of complications in individuals with long-standing IDDM.| vauthors = Sell DR, Lapolla A, Odetti P, Fogarty J, Monnier VM | journal=Diabetes|date= Oct 1992|volume= 41|issue=10|pages= 1286–92| url=http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=166362| accessdate=2007-12-15 |doi=10.2337/diabetes.41.10.1286 |pmid=1397702}} 3 : Biomolecules|Guanidines|Imidazopyridines |
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